Lessons from the Woman Who Built Squarespace’s Customer Care Team from 1 to 184

If building a company were like planning a wedding, customer service is frequently the second cousin who’s invited when slots open up on the attendee list. Many believe that it's not as critical to success as sales and product development. The reality is that customer care is your most direct line to customers and has the power to define your brand. Users equate its voice with your company’s voice. At peak times, it represents your organization up to 60 times an hour — literally every minute. Christa Collins, ShopKeep's VP of Customer Care understands this value; if her experience stands for anything, it’s that customer care is a vital early priority.

Collins was the first customer service employee at website builder Squarespace. Over her tenure, she built the customer care team from one employee (her) to a division of 184 people operating across three time zones. She designed a workflow to triage 25,000 customer support requests per week — and that was only via its email channel. Now Collins is applying the lessons she learned to build the customer care division at ShopKeep, a cloud-based iPad point-of-sale system.

People who work in customer care need to be adept ambassadors; they must speak on behalf of their company to the customer and flip the model to represent the customer back to the company. The best in customer care are functional chameleons, becoming conversant as product managers, marketers and salespeople to bring resolution to customers. In this exclusive interview, Collins shares her sage advice on assembling a great customer care team, best practices for keeping customers happy and measuring performance in this essential but (too) often overlooked area.

Why Customer Care Matters Early

For Collins, the trigger for establishing customer care is simple. The moment you’ve got a product that people are going to use, you’ll have people who will want talk to you about it. “So much startup advice is growth stage specific, but launching customer care in parallel with a product is universal,” says Collins. “It doesn’t matter if you’re a really small startup. Someone must own the relationship and the information that the customer will relay to you.”

This notion holds true for even the most intuitive, human-centric products. This year, Apple retail chief Angela Ahrendts is reportedly revamping Apple’s Genius Bars to include walk-ins, SMS progress updates and other updates to its customer service, marking one of the more significant overhauls to Apple’s retail operations in years. “The lifespan of customer care should be that of the company’s first product — it begins when it does and doesn’t stop,” says Collins.

Establishing customer care early is a very public gesture. It broadcasts: we plan to invest as much when the product is in your hands, as we do when it’s in ours.

Throughout her career, Collins has observed that most initial customer care hires land between employee #5 and #10. It might seem premature, but if you’re pre-product, you should start identifying who’ll be the first member of your customer care team, with a goal to have the hire in place when your product launches.

“This does several things,” says Collins. “First, it creates a core team. You've got engineers, product and the bridge to the customer: customer service. It also creates a customer-centric culture from the beginning. Many companies launch a product and then ask how to be more customer service-oriented. Do it from the start, and you won’t deal with that question down the line.”

How to Catch-up If You Begin Customer Care Later

If you’re like most early-stage companies, you might not have considered or acted on building your customer care function in parallel with your product. If you’ve just brought on your first hire or early team members, encourage them to use this cheat sheet from Collins:

Ask why like a three-year old.Instinct comes from habit. Wisdom stems from context. Your customer care team will need both, and the only way they’ll get them is by channeling Simon Sinek and asking why first and often. Here’s a starter kit of “why” questions to get the background needed to serve customers:

To everyone: Why did this change? Why is this changing? Why didn’t that change?

To product/engineering: Why is this better for the customer? Why is this important now? Why is this the direction we’re going?

To sales/marketing: Why have we sold it in this way? Why do we target this customer and not that customer? Why do we now promote it the way we do?

To founders: Why is this our mission? Why is this our vision? Why is this the problem we solve? Why are we best equipped to deliver a solution?

Though she was a customer care veteran at Squarespace, Collins is still figuring out the history of and horizon for ShopKeep and its products. “Fearlessly and genuinely express your desire to understand,” says Collins, “Otherwise, people will assume that you’re up to speed and expect you to act knowledgeably. Asking why so often can be annoying if it’s challenging in nature rather than curious in spirit. But if you ask with respect and intent, you’ll get the history and hindsight you need without having had the experience firsthand.”

Ask why internally until you can start each answer to customers with: “Here’s why we did/do/will do this.”

Set up your primary channel and nail it.There are countless ways to connect with customers, from email to live chat, texts to tweets and phone to in-person support. “It’s especially hard to achieve excellent customer care across several channels as a small startup,” says Collins. “Pick a primary channel and provide great support experiences to your customers via that avenue alone. If you can consistently deliver to your standard for 3-6 months along that channel, then select and add another.”

Though Collins was a pioneering member of customer care at both Squarespace and ShopKeep, she developed different primary support channels at each.

“At Squarespace, we started with email communications and then live chat was introduced,” she says. “Here at ShopKeep it's primarily phone support and, now, email exists. We’ll continue to introduce more ways to serve customers down the road, but we’re methodical about attaining great service levels via a channel before adding another. Ultimately, whether it’s one or ten channels available, customers need to know that they’ll have a great experience regardless.”

After you choose your primary channel, it’s paramount to concurrently build in self-service. “Regardless of the primary channel you choose, always pair it with self-service. That should be your number one focus at all times,” says Collins. “Having a self-service option can address at least half of all requests in the early days. What’s more is that building it in conjunction with your primary channel is incredibly helpful, as self-service is fleshed out and fine-tuned through conversations with customers.”

Members of the ShopKeep Customer Care Team

Hire from your community.The first two hires after Collins joined Squarespace were active members in their online support forum and community. “There’s no better demonstration of qualifications,” she says. “In the forums, they showed great product knowledge, enthusiasm for our offering and a desire to interact with our team and other customers. To me, that was the interview. They were dialed in before we hired them. And I believe they’re both still with the company today.”

Those who share their time and expertise voluntarily typically come with a level of commitment that extends beyond the standard call of duty. “I knew the two of them would not only do their job well, but also be able to train new hires and be natural role models,” says Collins. “Also, they are seismic support when the foundation’s trembling. Once, I remember when our average inbound customer care requests instantly doubled after a product release. They were among the first to volunteer for a 14-hour shift, starting at the end of the work day. They just didn’t clock out.”

Start tiering when your team hits 20.As the company, product suite and number of features grow, so will your customer care team. Collins led a very informal, flat structure for a long time, but once her team hit twenty people, she started to put in a hierarchy. “One day, I walked into our part of the office and didn’t know everybody’s name. Can you imagine how mortifying that is to a customer care professional who prides herself on being personable and community-oriented? That’s when I formally created a level of managers.”

As products become more numerous and sophisticated, customer service must grow to mirror that complexity. Also, as the customer base becomes more familiar with the product, the requests and questions start to change. All these shifts require a more specialized and flexible customer care structure. “It’s the same with other departments. Customer care is a living, breathing creature that continues to evolve,” says Collins.

To build a tiered team to respond to these changes, Collins recommends the following structure:

Tier 1: These team members are your entry level customer support agents. They are on the front line, interacting directly with customers.

Tier 2: This is a level for specialists that deal with escalated issues. They also interface directly with product, engineering and other teams in the company.

Tier 3: This layer is for customer service managers, who oversee and optimize the performance of the other two tiers. As products shift and specialities are needed, this group can re-organize teams to make sure all key areas are covered.

As each company’s customer care resources and needs vary, Collins’ rule of thumb is to add someone to the team when you find yourself at a breaking point. “The reality for most companies will be a reactive approach to hiring for customer service. So when you’re operating at maximum pain and you can’t continue, it’s time to add more people,” says Collins. “However, when your customer service headcount is between 20-40 staff, you’ve gone through enough product and hiring cycles that you can start to reliably project how many you’ll need by quarter and year.”

Superb customer care translates into great word of mouth. The trust of your customer is not only what’s at stake; it’s the potential conviction of each customer’s network, too.

What It Means To Truly Care for Customers

There are standouts in customer service — Zappos, Amazon, Starbucks, and Eventbrite — but for Collins, her line of work starts and ends with how her team communicates with customers. Her school of thought prioritizes relationships built over resolutions tallied, becoming an expert decoder of customer cues and establishing a standard tone with an individual’s texture.

Care or Don’t Care. There is no Try.Calling it customer care, customer support, customer happiness or customer success is semantics in the end. However, whether you are primarily focused on customers OR their challenges is a nuance with important ramifications. “Those who ask how to create the feeling of caring for customers are typically focused primarily on issue resolution, while customers are more of an afterthought,” says Collins. “It’s easy to get hung up on metrics and KPIs, but I try to remind myself to shape the interaction with a customer to be a conversation, versus a response. It’s about listening to what they’re telling you, not waiting until you can give them an answer.”

For example, two years into her job at Squarespace, Collins felt in command of her work. She clocked fast response times because she was a quick typist and knew the answers to most every question she’d get. One day, a customer wrote in regarding a past due bill for his account, explaining that, as a freelancer, he was waiting on his client to complete his invoice to get paid. “He politely asked for an extension and it hit a chord. I know what it’s like to be tight on money,” says Collins. “And not only that, but he’s taking the time to write in and tell me his site is important to him. He’s asking for a couple of extra days versus just defaulting on his payment.”

Take a moment to ask yourself: will I take the opportunity to address more than what I’m being asked? In this case, Collins empathized with the customer, which allowed her to think more broadly and flexibly with her solution. She was not constrained by the problem presented to her. She could have just extended the due date, but instead said, “I’m just going to take care of your invoice. Don’t worry about it. It’s a free month. It’s fine.” Collins didn’t think much of it, but the customer wrote back, effusively expressing his gratitude. “It wasn't because I gave him a free month. It was because I said, ‘Hey, fellow human being, I care and can relate to your situation in some small way. I'd like to do something that would make your day a little bit easier."

Not everyone has someone ready to help who’s just an email or call away. I’m astonished by what people have shared with me. It’s a privilege to be entrusted with their vulnerability.

For all the Squarespace customers who have been touched by handwritten thank you cards or been sent flowers in the hospital, there are those who don’t want a relationship with a startup. How do you proceed then? “Sometimes they just want an answer. That happens,” says Collins. “And that's totally, absolutely fine. I think that you can create a relationship by not creating a relationship. The job really is being there in a way that the customer needs you to be when they need you to be there. So if they don't, then it’s your role to answer and then step back.”

Pinpoint and act on customer cues.Consistent and comprehensive customer care requires understanding subtle cues in both a written and verbal setting. Here are a few pointers from Collins on being mindful of what isn’t being said in your conversations with customers.

Lots of background noise. “If there’s a lot of ambient sound — a barking dog, footsteps, the rumble of a train or children’s voices, for example — please don't take up their time telling jokes or asking about their grandkids. They may be being polite, but they’re busy. Their time is as important as the answer. Speak clearly and move quickly.”

Non sequiturs and personal follow-up. “Verbose customers may be trying to soften you up to ask for a favor, but they also could be aiming for a real connection. It could be out of loneliness or interest. I recall customers that would always contact me before and after their vacations because we had talked about travel. It was great!”

Raised voice or curt notes. “Anger or frustration is generally easy to identify, but much harder to diffuse. I always try to think about anger as being passionate about a problem that a person can’t control but cares deeply about. When you see or hear it, you know. It’s best to provide structure to your response: playback what you’ve heard said and fix it immediately. If you can’t get it fixed quickly, lay out why and what you’ll do about it.”

That said, there are cases in which picking up on cues and caring about the customer will fail. Those instances — though rare — may require extracting yourself.

“Early in my career, when I was a manager at Nordstroms, a customer got very belligerent and started screaming in my face. It’s very intense emotionally when that happens. You can really hear a person's anger and malice towards you,” says Collins. “I froze. I wanted to make sure he was okay, talk him down and resolve the situation, but it was so abusive. I'll never forget when the store manager on call arrived and calmly asked me to go to the back room.”

The takeaway: if a line’s crossed and it's no longer a productive conversation, then there's no need to continue. The manager removed me from the situation and dealt with the angry customer. She knew I was not okay, but asked if I was, then said, “I want you to know, that’s never okay. You do not deserve to be spoken to or treated that way. You always have the resource of calling a supervisor if the situation becomes uncomfortable. That’s what we’re here for.” Collins has taken that lesson with her and ensures there’s always a lifeline for her customer service team. Content customers start with a happy customer care team — sometimes that takes shielding and protecting people from toxic customers.

Members of the Squarespace Customer Care Team

The company sets message and tone — individuals bring texture.Like many teams in most early-stage companies, customer service is closely influenced by the founders early on. “Looking back, especially at Squarespace, our customer service communications took on the voice of [founder and CEO] Anthony [Casalena] and our early engineers,” says Collins. “Then, over time, it evolved and the customer care team standardized how to support our customers and with which content. We direct the message and tone.”

For straightforward or strict actions like a DMCA takedown request or a terms of service violation, customer care teams shouldn’t deviate from prescribed language. But in many cases, Collins encourages her team members to communicate content with their own flair and personality. “That authenticity is essential to establishing an early connection with customers — and gives ownership to customer care representatives. Some may use more exclamation points, add in a personal greeting or sign-off in a formal way. The goal is to handle the communication so it’s in line with our script and tone, but also sounds like the individual.”

Collins’ background as a legal secretary has informed her personal communication style. “Back when I communicated with customers, my tone was very dry. My words were simple and to the point, and I was never excessive with punctuation,” says Collins. “It’s what you’d expect from someone who wrote emails to attorneys for years. It was comfortable for me, and I want the same for each person on my team. I’ll tell them: “Hey, this is how we answer this question. This is how we address this issue. Have at it. Just reply and use your voice.”

Various voices can be equally effective, but treat the customer’s replies as a mirror. “You can use an exclamation point to show enthusiasm without looking silly, but stay alert to how your customer receives it,” Collins says. “Can you connect with this person and speak in a conversationally casual way or are they expecting something else from you? Are they seeking a really quick response that's straight to the point and cut and dry? You need to make that determination and calibrate to your customer.”

Measuring the Effectiveness of Your Customer Care

When it comes to tools to evaluate customer support, there’s an alphabet soup of tools: NPS (Net Promoter Score), CSAT (Customer Satisfaction Score) and CES (Customer Effort Score), to name a few. Collins recommends ramping up slowly to more systematic methodologies and running your own tests to understand the makeup of your specific customer base. Here’s how:

Make it lightweight to start.There can be a tendency to get intricate with surveying customers about their experience, but Collins recommends keeping it simple at the beginning. “At the start, try to measure success in a very lightweight fashion — literally, click thumbs up or thumbs down to share if we helped you. This will help you get a sense of the value you’re giving and the rhythm with which you’re providing it,” she says.

It can become a lot more sophisticated down the road. Allowing for more free-form feedback will get you a bit more color, and you can start to figure out how to focus your resources. “If they say that it was a great interaction, but ask why they needed to write in to get it, it’s time to build out your FAQ. If they say you don't know what you’re talking about it, perhaps you should look into ongoing training for the team,” says Collins. “Maybe they’ll comment that the interface is terrible and you’ve made it difficult. While that's not necessarily reflective of the customer service performance itself, that's valuable feedback to pass along to Product or Engineering. Remember, you receive the report card for the entire class, not just you.”

Think beyond what you measure. Prioritize where and how, too.Collins sees a place for NPS and customer satisfaction measurement tools, but for different parts of the organization. “I think NPS is owned by the company, while customer satisfaction belongs to each department, including customer care. It tells us how if and how we are handling your requests,” she says. “However, NPS — if you’d recommend this product to a friend — receives a rating, in which customer service only plays a part.”

It’s equally important to run tests that measure your unique take on customer support. For example, while at Squarespace, Collins emphasized conversations over transactions. She had a hypothesis that, as in life, a conversation — and relationship — would become more valuable after many interactions. So, if customers wanted to keep asking questions, let them. Her team measured customer satisfaction by number of interactions. As this was over email support channel, each response on an email thread constituted one interaction. Here’s what they found:

2-4 interactions: low customer satisfaction

5-9 interactions: high customer satisfaction

10-18 interactions: low customer satisfaction

19+ interactions: moderate customer satisfaction

“Taken with the qualitative data, we found that a quick correspondence — even if we solved the problem — felt transactional or didn’t provide a long enough runway to show our value-add,” says Collins. “Between 5-9 interactions, customers felt that they were engaged in an experience that was informative and conversational. We could demonstrate that weren’t robots or outsourced support — we were real humans taking time to help.”

The biggest lesson emerged from the cases that involved ten or more interactions. “With the longer conversations, we realized that, by and large, we had messed up,” says Collins. “Something happened and we missed something. Maybe we didn’t pay attention. Or we overlooked a key piece of information or weren't reading properly. Obviously, those cases were really bad.”

Then, for the outlier segment of 19+ interactions, someone senior from customer service would typically step in to own the case. “They were really long emails, and the support lead would eventually turn the ship around,” says Collins. “They’d get it resolved. It might take five more back and forth emails, but the customer would get an answer and say something like, ‘You know, I was really, really mad at you, but you fixed it. Thank you and I'm happy. Next time, do better but at least you put in the effort. You took the time to own it and to make sure that it was resolved.’”

Squarespace's Customer Care Team

For a long time, customer care was deprioritized and often built in haste when the need arose. Then it was acknowledged, but seen as a necessary evil. Now, from Warby Parker to Zappos, companies have increasingly made customer care indispensable to — and sometimes synonymous with — their product and reputation. It’s a wise path forward that many companies still neglect. Savvy startups will launch customer care in parallel with their first product. If not, they’ll heed Collins’ tips in order to catch up quickly. Their departmental mission and metrics will value relationships over resolutions and conversations over transactions.

“At the end of the day, a customer care professional is benevolent double agent, acting on behalf of both the company and customer,” says Collins. “If forced to choose a side, they won’t. They’ll go rogue and represent the product because, like them, they were formed by the company for the benefit of the customer. They’ll always be of and between those worlds.”

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